Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
  • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/38—Nitrogen atoms
  • C07D215/42—Nitrogen atoms attached in position 4

Definitions

• R 1 , R 2 , R 3 , R 4 in each case independently of one another are hydrogen, hydroxyl, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkoxyalkyl,
• R 5 , R 6 in each case independently of one another are hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio;
• R 7 is hydrogen, C 1 -C 4 -alkyl, formyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl;
• R 8 is hydrogen, formyl, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl or C 1 -C 8 -alkylcarbonyl, it being possible for these groups to be partially or fully halogenated, C 3 -C 7 -cycloalkyl or C 3 -C 7 -cycloalkenyl, it being possible for these radicals to be partially or fully halogenated,
• aryl or hetaryl it being possible for these radicals to have attached to them one to three of the following groups: nitro, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfoxy, C 1 -C 4 -alkylsulfonyloxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylcarbonyloxy, C 1 -C 4 -alkoxycarbonyl, aryl, aryloxy;
• R 9 is aryl or hetaryl, it being possible for these radicals to have attached to them one to three of the following groups: nitro, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfoxy, C 1 -C 4 -alkylsulfonyloxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylcarbonyloxy, C 1 -C 4 -alkoxycarbonyl, aryl or aryloxy, where the cyclic substitu
• WO 94/07492 discloses 4-hydrazinoquinolines and 4-hydrazonoquinolines which are pharmaceutically active.
• the compounds of the present invention can be prepared by applying known syntheses.
• the starting compounds can be obtained by known methods.
• the compounds of the general formula I are obtained by subjecting the 4-chloroquinolines II to a condensation reaction with hydrazines of the formula III.
• the 4-chloroquinolines II are preferably reacted with the hydrazines in question at elevated temperatures in a suitable diluent.
• suitable diluents are inert organic solvents, such as aliphatic hydrocarbons, eg. petroleum ether, aromatic hydrocarbons, eg. toluene or o-, m- or p-xylene, or else alcohols, eg. n-, i- or t-butanol.
• the invention also encompasses the salts of the compounds I, in particular the salts of mineral acids or Lewis acids.
• the type of the salt is normally not critical. Preferred for the purposes of the invention are those salts which do not damage the plants, areas, materials or spaces to be kept free from harmful fungi and which do not adversely affect the activity of the compounds I.
• the salts of the compounds I are accessible in a manner known per se, for example by reacting the relevant quinolines I with acids in water or an inert organic solvent at from -80° to 120°, preferably 0° to 60° C.
• the invention also encompasses the N-oxides of the compounds I. They can be prepared by methods known from the literature (see, for example, Ann. Chim. Rome; 46(1956)1050).
• Suitable oxidants are inorganic and organic compounds, eg. peroxides, hypohalites, nitrous acid, nitric acid, metal salts, eg. Fe(III) salts, Cu(II) salts, Pb(IV) salts, but also oxygen or air.
• Suitable diluents are water, organic and inorganic acids, eg. glacial acetic acid, sulfuric acid or nitric acid; alcohols, eg. methanol or ethanol; halogenated hydrocarbons, aromatic hydrocarbons or else dimethylformamide.
• the reaction temperature is generally from 0° to the boiling point of the solvent in question.
• halogen fluorine, chlorine, bromine and iodine
• alkyl straight-chain or branched alkyl groups having 1 to 8 carbon atoms, eg. C 1 -C 6 -alkyl, such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1-eth
• haloalkyl, or partially or fully halogenated alkyl straight-chain or branched alkyl groups having 1 to 4 or 8 carbon atoms (as mentioned above), it being possible for the hydrogen atoms in these groups to be partially or fully replaced by halogen atoms (as mentioned above), eg.
• C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
• alkoxy straight-chain or branched alkoxy groups having 1 to 4 carbon atoms, eg. C 1 -C 3 -alkoxy, such as methyloxy, ethyloxy, propyloxy and 1-methylethyloxy;
• alkoxyalkyl straight-chain or branched alkyl groups having 1 to 8 carbon atoms (as mentioned above) which have attached to them in any position a straight-chain or branched alkoxy group (as mentioned above) having, in the case of C 1 -C 4 -alkoxyalkyl, 1 to 4 carbon atoms, such as methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl, 2-n-propoxyethyl and 2-butoxyethyl;
• haloalkoxy straight-chain or branched alkoxy groups having 1 to 4 carbon atoms (as mentioned above), it being possible for the hydrogen atoms in these groups to be partially or fully replaced by halogen atoms (as mentioned above), eg.
• C 1 -C 2 -haloalkoxy such as chloromethyloxy, dichloromethyloxy, trichloromethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, 2-chloro-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy, 2,2-dichloro-2-fluoroethyloxy, 2,2,2-trichloroethyloxy and pentafluoroethyloxy;
• alkylthio straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as mentioned above) which are bonded to the skeleton via a sulfur atom (--S--), eg. C 1 -C 4 -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, n-butylthio and tert-butylthio;
• alkoxycarbonyl straight-chain or branched alkoxy groups having 1 to 4 C atoms (as mentioned above) which are bonded to the skeleton via a carbonyl group (--CO--);
• alkenyl straight-chain or branched alkenyl groups having 2 to 8 carbon atoms and a double bond in any position, eg. C 2 -C 6 -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-buteny
• alkynyl straight-chain or branched alkynyl groups having 2 to 8 carbon atoms and a triple bond in any position, eg. C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-penty
• cycloalkyl monocyclic alkyl groups having 3 to 7 carbon ring members, eg. C 3 -C 7 -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl;
• cycloalkenyl monocyclic alkyl groups having 5 to 7 carbon ring members which contain one or more double bonds, eg. C 5 -C 7 -cycloalkenyl, such as cyclopentenyl, cyclohexenyl and cycloheptenyl;
• non-aromatic 4- to 8-membered rings which, besides carbon, additionally contain one or two oxygen, sulfur or nitrogen atoms as ring members, such as saturated 5- or 6-membered rings having 1 or 2 nitrogen and/or oxygen atoms, such as 3-tetrahydrofuranyl, 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-morpholinyl and 3-morpholinyl;
• aryl monocyclic or polycyclic aromatic groups having 6 to 10 C atoms, such as phenyl and naphthyl;
• arylalkyl aryl groups (as mentioned above) which, in the case of aryl(C 1 -C 4 )alkyl, are bonded to the skeleton via alkyl groups having 1 to 4 carbon atoms (as mentioned above), eg. phenyl(C 1 -C 4 )alkyl, such as benzyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 1-phenylethyl, 1-phenylpropyl and 1-phenylbutyl;
• aryloxy aryl groups (as mentioned above) which are bonded to the skeleton via an oxygen atom (--O--), such as phenoxy, 1-naphthoxy and 2-naphthoxy;
• hetaryl aromatic mono- or polycyclic radicals which, besides carbon ring members, can additionally contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, eg.:
• 5-membered hetaryl containing 1 to 3 nitrogen atoms 5-membered hetaryl ring groups which, besides carbon atoms, can contain 1 to 3 nitrogen atoms as ring members, eg. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl;
• 5-membered hetaryl containing 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur atom or oxygen atom or 1 oxygen or 1 sulfur atom 5-membered hetaryl ring groups which, besides carbon atoms, can contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom or 1 oxygen or sulfur atom as ring members, eg.
• 5-membered hetaryl containing 1 to 3 nitrogen atoms or 1 nitrogen atom and/or one oxygen or sulfur atom 5-membered hetaryl ring groups which, besides carbon atoms, can contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom or 1 oxygen or one sulfur atom as ring members and in which 2 adjacent carbon ring members or 1 nitrogen and 1 adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group;
• 5-membered hetaryl bonded via nitrogen and containing 1 to 4 nitrogen atoms, or benzo-fused 5-membered hetaryl bonded via nitrogen and containing 1 to 3 nitrogen atoms 5-membered hetaryl ring groups which, besides carbon atoms, can contain 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms, respectively, as ring members and in which 2 adjacent carbon ring members or one nitrogen and one adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the skeleton via one of the nitrogen ring members;
• 6-membered hetaryl containing 1 to 3, or 1 to 4, respectively, nitrogen atoms 6-membered hetaryl ring groups which, besides carbon atoms, can contain 1 to 3, or 1 to 4, respectively, nitrogen atoms as ring members, eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;
• 6-membered hetaryl containing 1 to 4 nitrogen atoms 6-membered hetaryl ring groups in which 2 adjacent carbon ring members can be bridged by a buta-1,3-diene-1,4-diyl group, eg. quinoline, isoquinoline, quinazoline and quinoxaline.
• partially or fully halogenated is to express that in groups which are thus characterized some or all of the hydrogen atoms can be replaced by identical or different halogen atoms as mentioned above.
• Alkylamino an amino group which has attached to it a straight-chain or branched alkyl group having 1 to 6 carbon atoms as mentioned above;
• dialkylamino an amino group which has attached to it two straight-chain or branched alkyl groups which are independent of one another and have attached to them in each case 1 to 6 carbon atoms as mentioned above;
• alkylcarbonyl straight-chain or branched alkyl groups having 1 to 10 carbon atoms which are bonded to the skeleton via a carbonyl group (--CO--);
• alkylsulfonyl straight-chain or branched alkyl groups having 1 to 6 or 10 carbon atoms which are bonded to the skeleton via a sulfonyl group (--SO 2 --);
• alkylsulfoxyl straight-chain or branched alkyl groups having 1 bis 6 carbon atoms which are bonded to the skeleton via a sulfoxyl group (--S( ⁇ O)--);
• alkylsulfonyloxy straight-chain or branched alkyl groups having 1 to 6 or 10 carbon atoms which are bonded to the skeleton via a sulfonyloxy group (--SO 2 --O);
• alkylcarbonyloxy straight-chain or branched alkyl groups having 1 to 10 carbon atoms which are bonded to the skeleton via a carbonyloxy group (--CO--O);
• alkoxycarbonyl straight-chain or branched alkyl groups having 1 bis 6 carbon atoms which are bonded to the skeleton via a oxycarbonyl group (--OC( ⁇ O)--).
• R 1 , R 2 , R 3 , R 4 in each case independently of one another are hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkoxyalkyl,
• R 5 and R 6 in each case independently of one another are hydrogen, C 1 -C 2 -alkyl or halogen
• R 7 and R 8 in each case independently of one another are hydrogen, C 1 -C 6 -alkyl, C 1 -C 3 -alkylcarbonyl, formyl
• R 7 , R 8 together are a bond
• R 9 is aryl or hetaryl, it being possible for these radicals to have attached to them one to three of the following groups: nitro, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfoxy, C 1 -C 4 -alkylsulfonyloxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylcarbonyloxy, C 1 -C 4 -alkoxycarbonyl, aryl or aryloxy, where the cyclic substituents, in turn, can have attached to them one to three
• Particularly preferred compounds I are those where the radicals have the following meanings, either on their own or in combinations:
• R 1 , R 2 , R 3 , R 4 are hydrogen
• R 3 cyano, halogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkyloxy, C 1 -C 3 -alkylthio, C 1 -C 3 -haloalkoxy; preferably halogen, C 1 -C 3 -alkyl, in particular chlorine and methyl;
• R 5 and R 6 are hydrogen, halogen, methyl, especially hydrogen
• R 5 is hydrogen, methyl, chlorine, especially hydrogen
• R 6 is hydrogen
• R 7 is hydrogen, methyl, formyl, C 1 -C 2 -alkylcarbonyl, especially hydrogen;
• R 7 and R 8 are hydrogen, C 1 -C 6 -alkyl, C 4 -C 6 -cycloalkyl, formyl, C 1 -C 2 -alkylcarbonyl;
• R 8 is hydrogen, formyl, C 1 -C 2 -alkylcarbonyl, C 1 -C 4 -alkyl, C 4 -C 6 -cycloalkyl; especially preferably hydrogen, formyl, CH 3 CO, C 1 -C 4 -alkyl; furthermore preferably hydrogen, C 1 -C 4 -alkyl, especially preferably hydrogen, methyl, ethyl, i-propyl, n-butyl, especially hydrogen;
• R 7 and R 8 especially preferably form a joint bond
• R 9 is aryl, it being possible for these radicals to have attached to them one to three of the following groups: nitro, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfoxy, C 1 -C 4 -alkylsulfonyloxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylcarbonyloxy, C 1 -C 4 -alkoxycarbonyl, aryl or aryloxy, where the cyclic substituents, in turn, can have attached to them one to three of the following substituents
• radicals preferably aryl, it being possible for these radicals to have attached to them one to three of the following groups: nitro, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, phenyl, phenyloxy.
• novel compounds of the formula I are suitable as fungicides.
• novel compounds can be employed for example in the form of ready-to-spray solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading or granules or by means of spraying, atomizing, dusting, spreading or pouring.
• ready-to-spray solutions powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading or granules or by means of spraying, atomizing, dusting, spreading or pouring.
• the use forms depend on the intended aims; in any case, they should guarantee the finest possible distribution of the active ingredients according to the invention.
• the plants are sprayed or dusted with the active ingredients, or the seeds of the plants are treated with the active ingredients.
• the formulations are prepared in a known manner, eg. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents and auxiliary solvents if water is used as the diluent.
• Auxiliaries which are suitable are essentially: solvents such as aromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg. methanol, butanol), ketones (eg. cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (eg.
• kaolins such as kaolins, clays, talc, chalk) and ground synthetic minerals (eg. highly-disperse silica, silicates); emulsifiers, such as non-ionic and anionic emulsifiers (eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose.
• non-ionic and anionic emulsifiers eg. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates
• dispersants such as lignosulfite waste liquors and methylcellulose.
• Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, eg. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids, with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated iso-octyl-, octy
• Powders, materials for spreading and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.
• Granules eg. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
• Solid carriers are mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powder or other solid carriers.
• V a mixture, ground in a hammer mill, of 80 parts by weight of a preferably solid compound I according to the invention, 3 parts by weight of sodium di-iso-butylnaphthalene- ⁇ -sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel; a spray mixture is obtained by finely distributing the mixture in water;
• IX a stable oily dispersion of 20 parts by weight of a compound I according to the invention, 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde condensate and 50 parts by weight of a paraffinic mineral oil.
• novel compounds are distinguished by an outstanding efficacy against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Deuteromycetes, Ascomycetes, Phycomycetes and Basidiomycetes. Some of them act systemically and can be employed as foliar- and soil-acting fungicides.
• the compounds are applied by treating the fungi, or the seeds, plants, materials or the soil to be protected against fungal infection, with a fungicidally active amount of the active ingredient.
• Application is effected before or after infection of the materials, plants or seeds with the fungi.
• novel compounds are specifically suitable for controlling the following plant diseases:
• Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, Uncinula necator in grapevines, Puccinia species in cereals, Rhizoctonia species in cotton and lawns, Ustilago species in cereals and sugar cane, Venturia inaequalis (scab) in apples, Helminthosporium species in cereals, Septoria nodorum in wheat, Botrytis cinerea (gray mold) in strawberries, grapevines, ornamentals and vegetables, Cercospora arachidicola in groundnuts, Pseudocercosporella herpotrichoides in wheat and barley, Pyricularia oryzae in rice, Phytophthora infestans in potatoes and tomatoes, Fusarium and Verticillium species in various plants, Plasmopara viticola in grapevine
• novel compounds can also be employed in the protection of materials (protection of wood), eg. against Paecilomyces variotii.
• the fungicidal compositions comprise from 0.1 to 95, preferably from 0.5 to 90, % by weight of active ingredient.
• the rates of application are from 0.025 to 2, preferably 0.1 to 1 kg, of active ingredient per ha.
• amounts of from 0.001 to 50, preferably 0.01 to 10 g, of active ingredient are generally required per kilogram of seed.
• the agents according to the invention can also be present together with other active ingredients, eg. herbicides, insecticides, growth regulators, fungicides or else fertilizers.
• a mixture with fungicides in many cases results in a widening of the fungicidal spectrum of action.
• sulfur, dithiocarbamates and their derivatives such as iron(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N'-propylenebisdithiocarbamate), zinc (N,N'-propylenebisdithiocarbamate), N,N'-polypropylenebis(thiocarbamoyl) disulfide;
• nitro derivatives such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethyl acrylate, 2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate, diisopropyl 5-nitro-isophthalate;
• heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1- bis(dimethylamino)-phosphinyl!-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo 4,5-b!quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(furyl-(2))benzimidazole, 2-(thiazolyl-(4))benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trich
• fungicides such as dodecylguanidine acetate, 3- 3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl!glutarimide, hexachlorobenzene, methyl N-(2,6-dimethylphenyl)-N-furoyl(2)-DL-alaninate, methyl N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-DL-alaninate, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone, methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)-DL-alaninate, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3- (3,5-dichlorophenyl)
• strobilurins such as methyl E-methoximino- ⁇ -(o-tolyloxy)-o-tolyl!acetate, methyl E-2- ⁇ 2- 6-(2-cyanophenoxy)pyridimin-4-yloxy!phenyl ⁇ -3-methoxyacrylate, N-methyl-E-methoximino- ⁇ -(2,5-dimethyloxy)-o-tolyl!acetamide.
• Anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl)aniline, N- 4-methyl-6-(1-propynyl)pyrimidin-2-yl!aniline, N-(4-methyl-6-cyclopropylpyrimidin-2-yl)aniline.
• Phenylpyrroles such as
• Cinnamamides such as
• the infected leaf area is indicated as a percentage.

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• 1996
  • 1996-09-04 TW TW085110812A patent/TW338038B/zh active
  • 1996-09-04 AU AU69870/96A patent/AU6987096A/en not_active Abandoned
  • 1996-09-04 JP JP9511623A patent/JPH11512406A/ja not_active Expired - Lifetime
  • 1996-09-04 US US09/029,740 patent/US5955473A/en not_active Expired - Fee Related
  • 1996-09-04 EP EP96931024A patent/EP0852579A1/de not_active Withdrawn
  • 1996-09-04 WO PCT/EP1996/003894 patent/WO1997010215A1/de not_active Application Discontinuation

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